Holiday Rentals in Middlebury, VT

76 available vacation rental offers

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Middlebury, VT holiday rentals
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Best Holiday rentals and Airbnb offers in Middlebury, VT

Top-Rated Holiday Rentals in the Old Town of Middlebury, VT

Reconnect deeply with your significant other at peaceful holiday rentals for couples in Middlebury, VT, offering romantic, quiet settings.

Downtown Middlebury 3 Br Home - Walk Everywhere! - Middlebury, VT
9.6 266 reviews

Downtown Middlebury 3 Br Home - Walk Everywhere!

apartment, Middlebury
This apartment is located in Middlebury, just a short walk from the National Museum of the Morgan Horse, Town Hall Theater, and Holy Cow Inc., with Henry Sheldon Museum of Vermont History and Middlebury College within a 1 kilometre walk. This property is highly rated, with excellent reviews for location, cleanliness, and overall experience.
The apartment has three bedrooms and one bathroom, offering 111 square metres of space. It comes with a fully equipped kitchen, a washing machine, a balcony, and a garden, making it a comfortable and convenient home away from home.
Updated Apartment Downtown - Middlebury, VT
10 46 reviews

Updated Apartment Downtown

apartment, Middlebury
This Middlebury apartment is ideally located within walking distance of Middlebury College and the town centre, offering easy access to shops, restaurants, and cultural attractions.
The recently renovated two-bedroom flat sleeps three guests, boasts a fully equipped kitchen including a dishwasher, and features high-quality bedding and linens; uncovered parking is available on the property.
Graduation, Skiing, Hiking - Best In Town Location - Middlebury, VT
9.7 69 reviews

Graduation, Skiing, Hiking - Best In Town Location

house, Middlebury
This Middlebury duplex is conveniently located downtown, within walking distance of Middlebury College, the Coop grocery store, and Royal Oak Coffee.
The recently remodelled two-bedroom property sleeps three, boasts a well-equipped kitchen with dishwasher, offers on-site parking for two cars, and provides complimentary tea, coffee, and oatmeal; nearby attractions include Lake Dunmore (24km), The Snow Bowl (32km), and Killington/Mad River Glen ski resorts (72km).
The Barn At Middlebury - Middlebury, VT
10 213 reviews

The Barn At Middlebury

apartment, Middlebury
This charming, renovated barn conversion is situated just outside Middlebury's village centre, a 1.6km walk from the town and a 2.4km walk from Middlebury College. The property has received excellent ratings for location, cleanliness, and overall experience.
This self-catering property offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. The apartment is fully equipped with modern amenities, including a dishwasher, washer/dryer, and a Nespresso coffee machine, and boasts a private terrace, a screened porch with a fireplace, and a private entrance with parking for up to three vehicles.

Best Middlebury, VT holiday rentals with air conditioning

Purple Door Cottage In The Heart Of Middlebury! - Middlebury, VT
10 2 reviews

Purple Door Cottage In The Heart Of Middlebury!

apartment, Middlebury
This Middlebury flat is located on a quiet side street, a mere 100 metres from Fire & Ice restaurant and one block from the town green, offering convenient access to the College campus and train station.
Spanning 139 square metres, this property accommodates up to six guests with two bedrooms and two bathrooms, featuring a great room with a workspace, a well-equipped kitchen, a family room, and a deck with a grill and fire ring, plus one on-site parking space.
Close To College-cheerful, Quiet, 2 Bedroom Home - Middlebury, VT
10 129 reviews

Close To College-cheerful, Quiet, 2 Bedroom Home

apartment, Weybridge
This recently renovated apartment is located just 2.4 kilometres from Middlebury College in Middlebury, Vermont, a charming town with shops, restaurants and cultural attractions. The apartment enjoys excellent ratings for location, cleanliness and user experience.
The apartment is comfortably furnished and can accommodate up to 4 guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden and parking, making it a great choice for families and groups.
Middlebury Bungalow - Middlebury, VT
10 22 reviews

Middlebury Bungalow

apartment, Middlebury
This two-bedroom flat in Middlebury is centrally located in a quiet neighbourhood near the woods, offering convenient access to downtown dining and activities, and is within walking distance of local shops.
This accommodation for up to four guests includes a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, parking, a dedicated office space, and keypad entry, making it an ideal base for skiing, running, and biking the Trail Around Middlebury.
Bluebird Studio-
Light Filled And Airy - Middlebury, VT
10 188 reviews

Bluebird Studio- Light Filled And Airy

apartment, Middlebury
This Middlebury self-catering apartment is situated just over 1.6km from the town centre, offering easy access to Middlebury's shops and restaurants.
The 51-square-metre studio features a queen-size bed, a dining area, and an adjoining dressing room, accommodating up to four guests and including a private garden and ample parking.

Frequently asked questions about holiday rentals in Middlebury, VT

  • What are some interesting places to visit in or near Middlebury, VT?

    Middlebury is a charming town with plenty to see and do. You can visit the beautiful Middlebury College campus, explore the Sheldon Museum, or take a scenic drive along the scenic Route 7. Just a short drive away, you can find the charming town of Brandon, home to the Vermont Marble Quarry and the Brandon Historical Society Museum.
  • What are the best Airbnb and holiday rentals in Middlebury, VT?

  • Which walking or cycling routes are the best in Middlebury, VT?

    The Otter Creek Trail is a popular choice for both walking and cycling, offering stunning views of the Green Mountains. For a shorter walk, try the Middlebury Village Green, a lovely park in the heart of town. If you're looking for a more challenging ride, the Route 7 scenic byway offers beautiful views and rolling hills.
  • What are the most popular Airbnbs in Middlebury, VT?

  • What sports or outdoor activites can visitors enjoy in and around Middlebury, VT?

    Middlebury is a haven for outdoor enthusiasts. You can go hiking in the Green Mountains, kayaking on Lake Champlain, or skiing at the nearby Snow Bowl. For a more relaxed experience, you can go fishing on the Otter Creek or take a scenic bike ride along the Route 7 scenic byway.
  • What are the best rentals for families and kids in Middlebury, VT?

    The best rentals for families and kids in Middlebury, VT are The Barn At Middlebury, Private Apartment In Middlebury and The Cottage Apartment In Downtown Middlebury.

  • What other towns or cities can be easily accessed from Middlebury, VT?

    From Middlebury, you can easily reach Burlington, Vermont's largest city, which is about a 45-minute drive away. The charming town of Vergennes, known for its historic architecture, is just a 15-minute drive from Middlebury. Also, a short drive away is the town of Rutland, known for its historic downtown and its proximity to the Green Mountains.
  • What are the best rentals or Airbnbs with a jacuzzi in Middlebury, VT?

    The best holiday rental or Airbnb with a jacuzzi in Middlebury, VT is Middlebury - Vt Newly Renovated Four Bedroom Luxury Home (Sleeps 8).

  • What amenities are commonly available in vacation rentals in Middlebury, VT?

    Vacation rentals in Middlebury typically offer a range of amenities, including fully equipped kitchens, comfortable living spaces, and laundry facilities. Many also include private decks or patios, perfect for enjoying the beautiful scenery. Some rentals even offer hot tubs or fireplaces for added comfort.
  • What time of year is best to rent a vacation rental Middlebury, VT?

    The best time to visit Middlebury depends on your interests. Summer is ideal for outdoor activities, while autumn offers stunning foliage. Winter brings snow sports and a charming, cozy atmosphere. Spring is a beautiful time to witness the rebirth of nature.
  • What are the local dishes in Middlebury, VT region?

    The local cuisine in Middlebury reflects the region's agricultural heritage. You'll find plenty of fresh, locally sourced ingredients, including maple syrup, cheddar cheese, and Vermont-grown apples. Try a classic New England clam chowder or a hearty Vermont-style stew. Don't forget to sample the local craft beers and wines.

Popular destinations

Check Out Holiday Rentals with a Balcony in Middlebury, VT

Private balconies with city skyline views come as standard at these holiday rentals in Middlebury, VT for a lovely start to your day.

Purple Door Cottage In The Heart Of Middlebury! - Middlebury, VT
10 2 reviews

Purple Door Cottage In The Heart Of Middlebury!

apartment, Middlebury
This Middlebury flat is located on a quiet side street, a mere 100 metres from Fire & Ice restaurant and one block from the town green, offering convenient access to the College campus and train station.
Spanning 139 square metres, this property accommodates up to six guests with two bedrooms and two bathrooms, featuring a great room with a workspace, a well-equipped kitchen, a family room, and a deck with a grill and fire ring, plus one on-site parking space.
Downtown Middlebury 3 Br Home - Walk Everywhere! - Middlebury, VT
9.6 266 reviews

Downtown Middlebury 3 Br Home - Walk Everywhere!

apartment, Middlebury
This apartment is located in Middlebury, just a short walk from the National Museum of the Morgan Horse, Town Hall Theater, and Holy Cow Inc., with Henry Sheldon Museum of Vermont History and Middlebury College within a 1 kilometre walk. This property is highly rated, with excellent reviews for location, cleanliness, and overall experience.
The apartment has three bedrooms and one bathroom, offering 111 square metres of space. It comes with a fully equipped kitchen, a washing machine, a balcony, and a garden, making it a comfortable and convenient home away from home.

Discover Family-Friendly Self-Catering Rentals in Middlebury, VT

Choosing a holiday rental built for families in Middlebury, VT means city attractions are close by for a much smoother trip.

Updated Farmhouse Minutes From Middlebury - Middlebury, VT
10 38 reviews

Updated Farmhouse Minutes From Middlebury

apartment, Weybridge
This Weybridge farmhouse, situated on Sheep Farm Road, is just over 1.6km from Middlebury town centre and Middlebury College, offering convenient access to local amenities.
The three-bedroom property, renovated in 2022, boasts an open-plan kitchen, dining, and living area, a large garden with firepit and deck, parking for three vehicles, and sleeps up to six guests.

Compare Holiday Rentals with Parking in Middlebury, VT

A car park at your holiday rental in Middlebury, VT means exploring the city centre is easy every day with no extra faff. Find your perfect stay.

South Street Retreat
Walk To Campus/town - Middlebury, VT
10 24 reviews

South Street Retreat Walk To Campus/town

apartment, Middlebury
Cozy House 4 Bedroom 3 Bath With Mountain Views - Middlebury, VT
10 50 reviews

Cozy House 4 Bedroom 3 Bath With Mountain Views

apartment, Cornwall
Modern Apartment 1 In Middlebury - Middlebury, VT
10 46 reviews

Modern Apartment 1 In Middlebury

apartment, Middlebury
New England Chalet  Champlain Valley - Middlebury, VT
10 1 review

New England Chalet Champlain Valley

apartment, Middlebury

Explore 5-Star Self-Catering Rentals in Middlebury, VT

Staying in a luxury holiday rental or Airbnb in Middlebury, VT ensures every detail of your trip feels considered. Enjoy high-end finishes and prime locations.

Midd Manor - Middlebury, VT
9.9 27 reviews

Midd Manor

apartment, Middlebury

Top Pet-Friendly Holiday Rentals in Middlebury, VT

Bringing your dog to Middlebury, VT? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.

The Middlebury Cottage - Middlebury, VT
9.8 104 reviews

The Middlebury Cottage

apartment, Middlebury
Cozy Apartment  Minutes To Middlebury - Middlebury, VT
9.7 216 reviews

Cozy Apartment Minutes To Middlebury

apartment, Middlebury

Choose the Right Holiday Rentals with a Pool in Middlebury, VT

Having a pool at your holiday rental in Middlebury, VT opens up a proper swim in the heart of the city without extra planning. Start comparing.

Purple Door Cottage In The Heart Of Middlebury! - Middlebury, VT
10 210 reviews

Purple Door Cottage In The Heart Of Middlebury!

house, Middlebury

Guest-Favourite Holiday Rentals with a Hot Tub in Middlebury, VT

Private hot tub access after a day in the city is one of those details that makes a trip to Middlebury, VT truly memorable.

The Middlebury Cottage · 4 Br Modern Village Home · Hot Tub · Walk To Campus - Middlebury, VT
10 68 reviews

The Middlebury Cottage · 4 Br Modern Village Home · Hot Tub · Walk To Campus

apartment, Middlebury
Walk Everywhere And Enjoy A Historic Vermont Home - Middlebury, VT
9.9 109 reviews

Walk Everywhere And Enjoy A Historic Vermont Home

apartment, Middlebury